US3947516A - Novel aromatic aldehydes and process for preparing them - Google Patents
Novel aromatic aldehydes and process for preparing them Download PDFInfo
- Publication number
- US3947516A US3947516A US05/489,538 US48953874A US3947516A US 3947516 A US3947516 A US 3947516A US 48953874 A US48953874 A US 48953874A US 3947516 A US3947516 A US 3947516A
- Authority
- US
- United States
- Prior art keywords
- acid
- compound
- hydrogen
- carboxylic acid
- atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 title 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 27
- -1 quinazolone Chemical compound 0.000 claims abstract description 21
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 14
- 239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 13
- 229960004011 methenamine Drugs 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 7
- 239000011707 mineral Substances 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 239000000460 chlorine Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims abstract 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims abstract 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 229940106681 chloroacetic acid Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- 229940005605 valeric acid Drugs 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Chemical group 0.000 claims 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims 1
- 101001072067 Homo sapiens Proprotein convertase subtilisin/kexin type 4 Proteins 0.000 claims 1
- 108010022052 Proprotein Convertase 5 Proteins 0.000 claims 1
- 102100036371 Proprotein convertase subtilisin/kexin type 4 Human genes 0.000 claims 1
- 102100036365 Proprotein convertase subtilisin/kexin type 5 Human genes 0.000 claims 1
- 102100038946 Proprotein convertase subtilisin/kexin type 6 Human genes 0.000 claims 1
- 101710180552 Proprotein convertase subtilisin/kexin type 6 Proteins 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000049 pigment Substances 0.000 abstract description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 abstract description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract description 2
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 125000005518 carboxamido group Chemical group 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract description 2
- 239000004922 lacquer Substances 0.000 abstract description 2
- 230000003287 optical effect Effects 0.000 abstract description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004033 plastic Substances 0.000 abstract description 2
- 229920003023 plastic Polymers 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000002966 varnish Substances 0.000 abstract description 2
- 150000001299 aldehydes Chemical class 0.000 abstract 3
- AYPSHJCKSDNETA-UHFFFAOYSA-N 2-chloro-1h-benzimidazole Chemical compound C1=CC=C2NC(Cl)=NC2=C1 AYPSHJCKSDNETA-UHFFFAOYSA-N 0.000 abstract 1
- 101001022148 Homo sapiens Furin Proteins 0.000 abstract 1
- 101000701936 Homo sapiens Signal peptidase complex subunit 1 Proteins 0.000 abstract 1
- 102100030313 Signal peptidase complex subunit 1 Human genes 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 7
- 229930040373 Paraformaldehyde Natural products 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 229920002866 paraformaldehyde Polymers 0.000 description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IEJDOJHUOKGZIQ-UHFFFAOYSA-N 5-amino-3-(2-hydroxynaphthalene-1-carbonyl)-1H-benzimidazol-2-one Chemical compound C1=CC=C2C(C(=O)N3C(=O)NC4=CC=C(C=C43)N)=C(O)C=CC2=C1 IEJDOJHUOKGZIQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- GDVQOCRJAPVQLB-UHFFFAOYSA-N (3-amino-2-hydroxyphenyl)-naphthalen-1-ylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C3=CC=CC=C3C=CC=2)=C1O GDVQOCRJAPVQLB-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- HVAXPRLYMAWEBL-UHFFFAOYSA-N 4-chlorobenzimidazol-2-one Chemical compound ClC1=CC=CC2=NC(=O)N=C12 HVAXPRLYMAWEBL-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 101001128694 Homo sapiens Neuroendocrine convertase 1 Proteins 0.000 description 1
- 101000601394 Homo sapiens Neuroendocrine convertase 2 Proteins 0.000 description 1
- 101000828971 Homo sapiens Signal peptidase complex subunit 3 Proteins 0.000 description 1
- 101000979222 Hydra vulgaris PC3-like endoprotease variant A Proteins 0.000 description 1
- 101000979221 Hydra vulgaris PC3-like endoprotease variant B Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102100032132 Neuroendocrine convertase 1 Human genes 0.000 description 1
- 102100037732 Neuroendocrine convertase 2 Human genes 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B55/00—Azomethine dyes
Definitions
- the present invention relates to novel aldehydes of 2-hydroxy-naphthalene-3-carboxylic acid arylides of the general formula I ##SPC2##
- X stands for a hydrogen, chlorine or bromine atom
- Ar stands for a naphthyl group, a phenyl group which may carry one to three lower alkyl, lower alkoxy, lower alkylsulfonyl, lower carbalkoxy, halogen, trifluoromethyl, nitro, cyano, lower alkanoylamino, carboxamido or sulfoamido groups, a benzimidazolone, chlorobenzimidazolone, quinazolone, quinoxaline, phthalimide or phthalazine group.
- the present invention moreover relates to a process for preparing these aldehydes, wherein a 2-hydroxy-naphthalene-3-carboxylic acid arylide of the general formula II ##SPC3##
- the starting compound is dissolved or suspended, generally, in two to ten times its amount of an aliphthatic carboxylic acid and the solution or suspension is heated for a prolonged time to temperature of up to 120°C, preferably from 80° to 100°C, the addition of a small amount of a mineral acid, such as sulfuric acid or hydrochloric acid being necessary except for trifluoroacetic acid used as the carboxylic acid.
- the acid may be added directly in admixture with the carboxylic acid or subsequently.
- Suitable lower carboxylic acids are, above all, acetic acid, but also propionic acird, butyric acid or valeric acid, moreover, dicarboxylic acids, such as adipic acid or malonic acid, or halogenated fatty acids, such as chloroacetic acid, trichloroacetic acid or trifluoroacetic acid.
- Hexamethylene tetramine may also be replaced by a likewise reacting mixture of ammonia and formaldehyde, these two components being used in an aqueous solution or in gaseous state.
- Hexamethylene tetramine is employed in a stoichiometric amount or in a small excess.
- paraformaldehyde may also be used in a molar ratio of 1:1 to 3:1, calculated on the starting compound.
- aldehydes of the invention are obtained with a good yield and in high purity.
- These aldehydes are valuable intermediate products for the synthesis of optical brighteners, pharmaceuticals and, in particular, of azamethine pigments which are obtained by condensation of these aldehydes with suitable amines, for example with aniline which may carry 1 to 3 chlorine or bromine atoms, methyl, ethyl, methoxy, ethoxy, nitro, alkyl- or arylsulfonyl groups.
- the pigments thus obtained are distinguished by good fastness properties and are especially suitable for the printing of paper and the coloring of lacquers, varnishes and plastics.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/670,997 US4074053A (en) | 1973-07-20 | 1976-03-26 | Aldehydes of 2-hydroxy-naphthalene-3-carboxylic acid arylides |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DT2337023 | 1973-07-20 | ||
| DE2337023A DE2337023C3 (de) | 1973-07-20 | 1973-07-20 | Verfahren zur Herstellung von Aldehyden von 2-Hydroxynaphthalin-3-carbonsäurearylamiden |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/670,997 Division US4074053A (en) | 1973-07-20 | 1976-03-26 | Aldehydes of 2-hydroxy-naphthalene-3-carboxylic acid arylides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3947516A true US3947516A (en) | 1976-03-30 |
Family
ID=5887576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/489,538 Expired - Lifetime US3947516A (en) | 1973-07-20 | 1974-07-18 | Novel aromatic aldehydes and process for preparing them |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3947516A (pt) |
| JP (1) | JPS5822472B2 (pt) |
| BE (1) | BE817946A (pt) |
| BR (1) | BR7405953D0 (pt) |
| CA (1) | CA1037480A (pt) |
| CH (1) | CH602601A5 (pt) |
| DE (1) | DE2337023C3 (pt) |
| FR (1) | FR2237880B1 (pt) |
| GB (1) | GB1459543A (pt) |
| IT (1) | IT1033083B (pt) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994015906A1 (en) * | 1993-01-15 | 1994-07-21 | Agouron Pharmaceuticals, Inc. | Hiv protease inhibitors and their preparation |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2441092C3 (de) * | 1974-08-28 | 1980-11-20 | Hoechst Ag, 6000 Frankfurt | Azamethin-Metallkomplex-Pigmente, Verfahren zu ihrer Herstellung und ihre Verwendung |
| JPS5817158A (ja) * | 1981-07-23 | 1983-02-01 | Dainippon Ink & Chem Inc | 紫外線を遮断する樹脂組成物 |
| JPH0432273U (pt) * | 1990-07-13 | 1992-03-16 | ||
| JP4971704B2 (ja) * | 2006-07-05 | 2012-07-11 | 上野製薬株式会社 | ナフトアルデヒド誘導体およびその製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1279257B (de) | 1963-12-04 | 1968-10-03 | Basf Ag | Verfahren zur Herstellung von Pigmentfarbstoffen |
-
1973
- 1973-07-20 DE DE2337023A patent/DE2337023C3/de not_active Expired
-
1974
- 1974-07-17 CH CH981474A patent/CH602601A5/xx not_active IP Right Cessation
- 1974-07-18 IT IT25340/74A patent/IT1033083B/it active
- 1974-07-18 BR BR5953/74A patent/BR7405953D0/pt unknown
- 1974-07-18 GB GB3189274A patent/GB1459543A/en not_active Expired
- 1974-07-18 JP JP49081779A patent/JPS5822472B2/ja not_active Expired
- 1974-07-18 US US05/489,538 patent/US3947516A/en not_active Expired - Lifetime
- 1974-07-19 CA CA205,223A patent/CA1037480A/en not_active Expired
- 1974-07-22 BE BE146818A patent/BE817946A/xx unknown
- 1974-07-22 FR FR7425367A patent/FR2237880B1/fr not_active Expired
Non-Patent Citations (3)
| Title |
|---|
| Chem. Abs., 51 5022-5024 (1957) Turitsyana et al. * |
| Chem. Abs., 53, 3709g (1959)--Kracker et al. * |
| choubal et al., J. Indian Chem. Soc., 35, No. 12, 1958 pp. 860-864. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994015906A1 (en) * | 1993-01-15 | 1994-07-21 | Agouron Pharmaceuticals, Inc. | Hiv protease inhibitors and their preparation |
| US5714518A (en) * | 1993-01-15 | 1998-02-03 | Agouron Pharmaceuticals | HIV protease inhibitors and methods of making the same |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1033083B (it) | 1979-07-10 |
| FR2237880B1 (pt) | 1979-07-20 |
| JPS5822472B2 (ja) | 1983-05-09 |
| CH602601A5 (pt) | 1978-07-31 |
| FR2237880A1 (pt) | 1975-02-14 |
| JPS5093955A (pt) | 1975-07-26 |
| DE2337023B2 (de) | 1979-01-18 |
| BE817946A (fr) | 1975-01-22 |
| DE2337023A1 (de) | 1975-02-20 |
| GB1459543A (en) | 1976-12-22 |
| BR7405953D0 (pt) | 1975-05-13 |
| DE2337023C3 (de) | 1979-09-06 |
| CA1037480A (en) | 1978-08-29 |
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